Tags

Type your tag names separated by a space and hit enter

Indole Alkaloids from Chaetomium globosum.
J Nat Prod. 2015 Jul 24; 78(7):1479-85.JN

Abstract

Two new indole alkaloids chaetocochin J (1) and chaetoglobinol A (8), along with chetomin (2), chetoseminudin A (3), cochliodinol (9), and semicochliodinol (10), were isolated from the rice culture of the fungus Chaetomium globosum. Their structures were elucidated by spectral analysis. Three new epipolythiodioxopiperazines, chaetocochins G-I (5-7), were identified by the combination of UPLC and mass spectrometric analysis. Chaetocochin I contained two sulfur bridges, one formed by three sulfur atoms between C-3 and C-11a, and the other formed by four sulfur atoms between C-3' and C-6'. Chaetocochin I was readily transformed into chetomin (2), chetoseminudin A (3), chaetocochin D (4), chaetocochin G (5), and chaetocochin H (6) by losing sulfur atoms. Compounds 1-3, and 8 exhibited antibacterial activities against Bacillus subtilis with MICs of 25, 0.78, 0.78, and 50 μg/mL, respectively, but not against Gram-negative bacterium (Escherichia coli). Compounds 2 and 8 were inactive against Candida albicans, Fusarium graminearum, Fusarium vasinfectum, Saccharomyces cerevisiae, and Aspergillus niger even at the high concentrations of 200 and 100 μg/mL, respectively. Compound 8 showed free radical scavenging capacity against the 1,1-diphenyl-2-picryl-hydrazyl (DPPH) and 2,2'-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid radical (ABTS(+•)), with IC50 values of 143.6 and 45.2 μM, respectively. The free radical scavenging capacity rates of compounds 1-3 on the DPPH and ABTS(+•) were less than 20% at the test concentrations (89.9-108.3 μM). The superoxide anion radical scavenging assay indicated that compounds 1-3, and 8 showed 14.8% (90.9 μM), 18.1% (90.9 μM), 51.5% (88.3 μM), and 30.4% (61.3 μM) superoxide anion radical scavenging capacity, respectively.

Authors+Show Affiliations

†Key Laboratory of Environmental and Applied Microbiology, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, People's Republic of China. ‡School of Pharmacy, Guiyang Medical College, Guiyang, Guizhou 550004, People's Republic of China.§State Key Laboratory of Biotherapy/Collaborative Innovation Center of Biotherapy, West China Hospital, Sichuan University, Chengdu, 610041, People's Republic of China.†Key Laboratory of Environmental and Applied Microbiology, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, People's Republic of China.†Key Laboratory of Environmental and Applied Microbiology, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, People's Republic of China.†Key Laboratory of Environmental and Applied Microbiology, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, People's Republic of China.†Key Laboratory of Environmental and Applied Microbiology, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, People's Republic of China.†Key Laboratory of Environmental and Applied Microbiology, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, People's Republic of China.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

26125976

Citation

Xu, Guo-Bo, et al. "Indole Alkaloids From Chaetomium Globosum." Journal of Natural Products, vol. 78, no. 7, 2015, pp. 1479-85.
Xu GB, He G, Bai HH, et al. Indole Alkaloids from Chaetomium globosum. J Nat Prod. 2015;78(7):1479-85.
Xu, G. B., He, G., Bai, H. H., Yang, T., Zhang, G. L., Wu, L. W., & Li, G. Y. (2015). Indole Alkaloids from Chaetomium globosum. Journal of Natural Products, 78(7), 1479-85. https://doi.org/10.1021/np5007235
Xu GB, et al. Indole Alkaloids From Chaetomium Globosum. J Nat Prod. 2015 Jul 24;78(7):1479-85. PubMed PMID: 26125976.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Indole Alkaloids from Chaetomium globosum. AU - Xu,Guo-Bo, AU - He,Gu, AU - Bai,Huan-Huan, AU - Yang,Tao, AU - Zhang,Guo-Lin, AU - Wu,Lin-Wei, AU - Li,Guo-You, Y1 - 2015/06/30/ PY - 2015/7/1/entrez PY - 2015/7/1/pubmed PY - 2015/10/24/medline SP - 1479 EP - 85 JF - Journal of natural products JO - J Nat Prod VL - 78 IS - 7 N2 - Two new indole alkaloids chaetocochin J (1) and chaetoglobinol A (8), along with chetomin (2), chetoseminudin A (3), cochliodinol (9), and semicochliodinol (10), were isolated from the rice culture of the fungus Chaetomium globosum. Their structures were elucidated by spectral analysis. Three new epipolythiodioxopiperazines, chaetocochins G-I (5-7), were identified by the combination of UPLC and mass spectrometric analysis. Chaetocochin I contained two sulfur bridges, one formed by three sulfur atoms between C-3 and C-11a, and the other formed by four sulfur atoms between C-3' and C-6'. Chaetocochin I was readily transformed into chetomin (2), chetoseminudin A (3), chaetocochin D (4), chaetocochin G (5), and chaetocochin H (6) by losing sulfur atoms. Compounds 1-3, and 8 exhibited antibacterial activities against Bacillus subtilis with MICs of 25, 0.78, 0.78, and 50 μg/mL, respectively, but not against Gram-negative bacterium (Escherichia coli). Compounds 2 and 8 were inactive against Candida albicans, Fusarium graminearum, Fusarium vasinfectum, Saccharomyces cerevisiae, and Aspergillus niger even at the high concentrations of 200 and 100 μg/mL, respectively. Compound 8 showed free radical scavenging capacity against the 1,1-diphenyl-2-picryl-hydrazyl (DPPH) and 2,2'-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid radical (ABTS(+•)), with IC50 values of 143.6 and 45.2 μM, respectively. The free radical scavenging capacity rates of compounds 1-3 on the DPPH and ABTS(+•) were less than 20% at the test concentrations (89.9-108.3 μM). The superoxide anion radical scavenging assay indicated that compounds 1-3, and 8 showed 14.8% (90.9 μM), 18.1% (90.9 μM), 51.5% (88.3 μM), and 30.4% (61.3 μM) superoxide anion radical scavenging capacity, respectively. SN - 1520-6025 UR - https://www.unboundmedicine.com/medline/citation/26125976/Indole_Alkaloids_from_Chaetomium_globosum_ L2 - https://doi.org/10.1021/np5007235 DB - PRIME DP - Unbound Medicine ER -